(2R,3'S)-5'α-[(E)-5-(3-Furyl)-2-methyl-1-pentenyl]-1',2',3',3'aα,5',7'aβ-hexahydro-3-hydroxy-3'α,4,7'-trimethylspiro[furan-2(5H),4'-[4H]inden]-5-one

Base Information

• Chemical Name: (2R,3'S)-5'α-[(E)-5-(3-Furyl)-2-methyl-1-pentenyl]-1',2',3',3'aα,5',7'aβ-hexahydro-3-hydroxy-3'α,4,7'-trimethylspiro[furan-2(5H),4'-[4H]inden]-5-one
• CAS No.: 63555-48-6
• Molecular Formula: C25H32O4
• Molecular Weight: 396.52
• Mol file: 63555-48-6.mol

Synonyms:Ircinianin;(-)-ircinianin;

Chemical Property of (2R,3'S)-5'α-[(E)-5-(3-Furyl)-2-methyl-1-pentenyl]-1',2',3',3'aα,5',7'aβ-hexahydro-3-hydroxy-3'α,4,7'-trimethylspiro[furan-2(5H),4'-[4H]inden]-5-one

Chemical Property:

• PSA: 59.67000
• LogP: 5.91460

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3'S)-5'α-[(E)-5-(3-Furyl)-2-methyl-1-pentenyl]-1',2',3',3'aα,5',7'aβ-hexahydro-3-hydroxy-3'α,4,7'-trimethylspiro[furan-2(5H),4'-[4H]inden]-5-one

There total 38 articles about (2R,3'S)-5'α-[(E)-5-(3-Furyl)-2-methyl-1-pentenyl]-1',2',3',3'aα,5',7'aβ-hexahydro-3-hydroxy-3'α,4,7'-trimethylspiro[furan-2(5H),4'-[4H]inden]-5-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

ircinianin methyl ether (63555-47-5) → (-)-ircinianin (63555-48-6)

Guidance literature:

With sodium 1-propanethiolate; In N,N-dimethyl-formamide; for 0.666667h; Ambient temperature;

DOI:10.1021/jo961993f

Reference yield: 72.0%

5-[(5E,7E,9E)-13-Furan-3-yl-2,6,10-trimethyl-trideca-5,7,9-trien-(Z)-ylidene]-4-hydroxy-3-methyl-5H-furan-2-one (108742-77-4) → C25H32O4 (63555-48-6,108814-19-3)

Guidance literature:

In benzene; for 1h; Heating;

DOI:10.1016/S0040-4039(00)83911-8

Reference yield:

furan-3-carboxaldehyde (498-60-2) → (-)-ircinianin (63555-48-6)

Guidance literature:

Multi-step reaction with 14 steps

2: 96 percent / carbon tetrabromide, Ph₃P / CH₂Cl₂ / 0.33 h / 0 °C

3: 90 percent / hexamethylphosphoric acid triamide / 2 h / 15 °C

4: 1) MeMgSnBu₃, CuCN, 2) I₂, Na₂CO₃ / 1) THF, 0 deg C, 20 min, 2) 0 deg C

5: 95 percent / tetrabutylammonium chloride, K₂CO₃, Pd(OAc)2 / dimethylformamide / 3 h / Ambient temperature

6: 88 percent / DIBAL-H / CH₂Cl₂; hexane / 0.33 h / -78 °C

7: 95 percent / BaMnO₄ / CH₂Cl₂ / 6 h / Ambient temperature

8: PPh₃ / CH₂Cl₂ / 0 °C

9: LDA / tetrahydrofuran / 0.5 h / 0 °C

10: 1) MeMgSnBu₃, CuCN, 2) I₂, Na₂CO₃ / 1) THF, hexane, -20 deg C, 20 min, 2) CH₂Cl₂, 0 deg C

11: 60 percent / CrCl₂, NiCl₂ / dimethylsulfoxide / 18 h / Ambient temperature

12: 89 percent / DMAP, pyridine / CH₂Cl₂ / 1 h / Ambient temperature

13: 72 percent / Bu₃SnH, AIBN / benzene / 0.5 h / Heating

14: 90 percent / n-C₃H₇SNa / dimethylformamide / 0.67 h / Ambient temperature

With pyridine; chromium dichloride; dmap; palladium diacetate; barium permanganate; methylmagnesium tributylstannane; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl-ammonium chloride; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; triphenylphosphine; nickel dichloride; lithium diisopropyl amide; sodium 1-propanethiolate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo961993f

upstream raw materials:

ircinianin methyl ether

furan-3-carboxaldehyde

4-methoxy-3-methyl-2(5H)-furanone

3-(3-furanyl)propan-1-ol